Vacation Rental Guest Specialist

20 hours ago

Manila, National Capital Region, Philippines Better Talent Full time $9,000 - $10,200 per year

Location:
Remote

Schedule:
Evening Shift | 4 PM – 12 AM EST (40 hrs/week)

Compensation:
$750–$850/month

Who We Are
At UPKEY Rentals, we're redefining what it means to feel "at home" while away. Based in Gainesville, Florida, we manage a growing portfolio of thoughtfully designed vacation homes that prioritize comfort, style, and hospitality in every detail. Whether hosting a traveling nurse, a Gator football fan, or a family exploring Florida's freshwater springs, we deliver more than a stay — we create memorable, elevated guest experiences.

As one of the top-rated short-term rental operators in the region, we are known for our quality, care, and commitment to excellence. We're a small, nimble, and passionate team with big ambitions. If you're someone who thrives in an environment where you can make a real impact and grow alongside the business, keep reading.

The Role
We're looking for a Vacation Rental Guest Specialist who thrives on making people feel cared for. You'll be the friendly, reliable voice behind our guest communications — from pre-booking to checkout. You'll handle inquiries, resolve issues quickly, coordinate with field teams, and ensure each guest enjoys a seamless, memorable stay. This is a fast-paced, remote role ideal for someone with excellent written communication, STR (short-term rental) experience, and a knack for solving problems calmly and professionally.

Responsibilities - What You'll Do

  • Be the first point of contact for guests via Airbnb, Vrbo, , and direct bookings
  • Respond to messages quickly (within 10 minutes during your shift) with warmth, clarity, and professionalism
  • Troubleshoot real-time guest issues — Wi-Fi, lockouts, appliance questions, etc.
  • De-escalate complaints and offer proactive, thoughtful solutions
  • Coordinate with cleaners, maintenance, and vendors to resolve concerns quickly
  • Manage reservations and automate messaging across our property management platforms
  • Process guest charges, refunds, and folio adjustments as needed
  • Assist in compiling incident reports and documentation for insurance claims
  • Keep detailed records of all communications and issue resolutions
  • Flag high-risk reviews and help us improve continuously
  • Attend regular team meetings

Qualifications - What We're Looking For

  • 3+ years in a Short-Term Rental management company virtual assistant role
  • Familiar with platforms like Airbnb, Vrbo, , and property management software (Guesty preferred)
  • Proficient in Google Workspace (Docs, Sheets, Gmail, Calendar) and team tools like Loom, Slack, Notion, and Google Meet
  • Exceptional written and verbal English — friendly, clear, and professional
  • Proven track record of delivering excellent guest experiences and resolving problems under pressure
  • Organized, detail-oriented, and able to juggle multiple tasks at once
  • Self-motivated with strong time management skills
  • Fast, reliable internet (50+ Mbps) and a quiet, professional home workspace
  • Willing to work evenings, weekends, and holidays as needed

Bonus Points

  • Previous experience working with U.S.-based clients or companies
  • Management experience or worked in a Leadership role
  • Familiar with PMS automation logic and creating automations
  • Competency in OTA Listing Optimization

Why Join Upkey?

  • Join a small, tight-knit, high-performing team
  • Make a real impact in a company passionate about hospitality
  • Flexible, remote work
  • Opportunity to grow with a fast-scaling business

Apply now and help us deliver the kind of hospitality that makes people feel truly at home — wherever they are.

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